Methylparaben → 4-(2-Piperidinoethoxy)benzoic acid hydrochloride

HRID 1290035

반응식

HRID 1290035 반응식
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][CH:3]=1.Cl.[Cl:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+].C(OCCCCC)(=O)C>O>[ClH:13].[N:16]1([CH2:15][CH2:14][O:1][C:2]2[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

참가 물질

6

반응물 4

HCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 12348Amyl AcetateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochloride

생성물 1

HCID 57438354-(2-Piperidinoethoxy)benzoic acid hydrochloride

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a 125 mL 3 neck flask with mechanical stirring, condenser, and a heating apparatus consisting of an RTD probe hooked via a temperature controller to a heating mantle, the following were added: 7.61 g methyl 4-hydroxybenzoate, 11.05 g β-chloroethylpiperidine hydrochloride, 16.59 g powdered potassium carbonate, and 60 mL amyl acetate. The mixture was heated in an oil bath under nitrogen to 115° C.-120° C. for 4 hour. HPLC indicated that the reaction was complete. The mixture was then cooled to ambient temperature and 40 mL of deionized water were added to dissolve solids. The aqueous layer was separated and discarded and the water wash was repeated. 5 mL of the organic phase was removed as an analytical standard. 25 mL 8N hydrochloric acid was added to remaining organic phase to extract the intermediate. The layers were separated and the acidified aqueous layers returned to the reaction flasks. The organic phase was discarded. The aqueous phase was heated to 95° C. until HPLC indicated complete hydrolysis of the ester (about 4 hours). The mixtures were cooled to 0° C.-5° C. for 1 hour and filtered. The filter cakes were rinsed with acetone (approx. 25 mL) and dried. Yield -12.61 g (83.6% theoretical).

후처리

  1. additionthe following were added
  2. temperatureThe mixture was heated in an oil bath under nitrogen to 115° C.-120° C. for 4 hour
  3. dissolutionto dissolve solids
  4. customThe aqueous layer was separated
  5. washthe water wash
  6. custom5 mL of the organic phase was removed as an analytical standard
  7. addition25 mL 8N hydrochloric acid was added
  8. extractionto extract the intermediate
  9. customThe layers were separated
  10. temperatureThe aqueous phase was heated to 95° C. until HPLC
  11. customhydrolysis of the ester (about 4 hours)
  12. temperatureThe mixtures were cooled to 0° C.-5° C. for 1 hour
  13. filtrationfiltered
  14. washThe filter cakes were rinsed with acetone (approx. 25 mL)
  15. customdried

출처 및 근거

ORD 기록
ord-4701fe9c1b3c428b9f05a40d5e5fa31a
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05750688

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